Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organometallic compound and an organic light-emitting device including the same are provided. The organometallic compound is represented by Formula 1 below:

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2017-0128295, filed on Sep. 29, 2017, in the KoreanIntellectual Property Office, the disclosure of which is incorporatedherein in its entirety by reference.

BACKGROUND 1. Field

One or more embodiments relate to an organometallic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, as well as excellent characteristics interms of brightness, driving voltage, and response speed.

An example of such organic light-emitting devices may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transit from an excited stateto a ground state, thereby generating light.

The organic light-emitting devices may be applied to a variety ofdevices, for example, an authentication device or an electronic device.

SUMMARY

Aspects of the present disclosure are directed toward an organiclight-emitting device capable of emitting light of a near-infrared (NIR)region while having a low driving voltage, a high efficiency, and a longlifespan, and an organic light-emitting apparatus including the organiclight-emitting device.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to an embodiment of the present disclosure, an organometalliccompound is represented by Formula 1 below:

In Formula 1,

M is a transition metal;

L₁ may be a monovalent organic ligand;

two bonds selected from a bond between X₁ and M, a bond between X₂ andM, and a bond between L₁ and M may each be a coordinate bond, and athird bond thereof may be a covalent bond;

X₁ and X₂ may each independently be N or C;

A₁ to A₄ may each independently be a C₅-C₃₀ carbocyclic group or aC₁-C₆₀ heterocyclic group;

T₁ and T₂ may each independently be selected from*—N[(L₁₁)_(a11)-(R₁₁)_(b11)]—*′, *—B(R₁₁)—*′, *—P(R₁₁)—*′,*—C(R₁₁)(R₁₂)—*′, *—Si(R₁₁)(R₁₂)—*′, *—Ge(R₁₁)(R₁₂)—*′, *—S—*′, *—Se—*′,*—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₁₁)=*′, *═C(R₁₁)—*′,*—C(R₁₁)═C(R₁₂)—*′, *—C(═S)—*′, and *—C≡C—*′;

L₁₁ may be a single bond, a substituted or unsubstituted C₅-C₃₀carbocyclic group, or a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup;

a11 may be an integer from 0 to 3, wherein, when a11 is zero,*-(L₁₁)_(a11)-*′ may be a single bond;

when a11 is two or more, two or more L₁₁(s) may be identical to ordifferent from each other;

R₁₁ and R₁₂ may optionally be linked to a neighboring substituent in R₁to R₃ to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group;

a1 and a2 may each independently be 0, 1, 2, or 3, wherein, when a1 iszero, *-(T₁)_(a1)-*′ may be a single bond, and when a2 is zero,*-(T₂)_(a2)-*′ may be a single bond;

when a1 is two or more, two or more T₁(s) may be identical to ordifferent from each other, and when a2 is two or more, two or more T₂(s)may be identical to or different from each dther;

R₁ to R₄, R₁₁, and R₁₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂);

neighboring substituents in R₁ to R₄ may optionally be linked to form asubstituted or unsubstituted C₅-C₃₀ carbocyclic group or a substitutedor unsubstituted C₁-C₆₀ heterocyclic group;

b1 to b4 and b11 may each independently be an integer from 1 to 6,wherein, when b1 is two or more, two or more R₁(s) may be identical toor different from each other, when b2 is two or more, two or more R₂(s)may be identical to or different from each other, when b3 is two ormore, two or more R₃(s) may be identical to or different from eachother, when b4 is two or more, two or more R₄(s) may be identical to ordifferent from each other, and when b11 is two or more, two or moreR₁₁(s) may be identical to or different from each other;

at least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

According to another embodiment of the present disclosure, an organiclight-emitting device includes: a first electrode; a second electrodefacing the first electrode; and an organic layer between the firstelectrode and the second electrode, the organic layer including anemission layer and at least one of the organometallic compound.

According to another embodiment of the present disclosure, an apparatusincludes the organic light-emitting device. The apparatus may be, forexample, a light-emitting device, an authentication apparatus, or anelectronic apparatus.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawings in which:

FIG. 1 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 2 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 3 is a schematic view of an organic light-emitting device accordingto an embodiment; and

FIG. 4 is a schematic view of an organic light-emitting device accordingto an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, sothat this disclosure will be thorough and complete, and will fullyconvey the scope of the inventive concept to those skilled in the art.As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

An organometallic compound according to an embodiment is represented byFormula 1 below:

M in Formula 1 may be a transition metal. The term “transition metal” asused herein refers to elements belonging to groups 3 to 12 in theperiodic table.

In one embodiment, M in Formula 1 may be selected from Zn, Cu, Pt, andPd, but embodiments of the present disclosure are not limited thereto.For example, M in Formula 1 may be Pt or Pd.

In Formula 1, two bonds selected from a bond between X₁ and M, a bondbetween X₂ and M, and a bond between L₁ and M may each be a coordinatebond, and the other (i.e., a third bond) thereof may be a covalent bond.

In one embodiment, the bond between X₁ and M and the bond between X₂ andM may each be a coordinate bond, and the bond between L₁ and M may be acovalent bond, but embodiments of the present disclosure are not limitedthereto.

For example, the bond between X₁ and M and the bond between L₁ and M mayeach be a coordinate bond, and the bond between X₂ and M may be acovalent bond. For example, the bond between X₂ and M and the bondbetween L₁ and M may each be a coordinate bond, and the bond between X₁and M may be a covalent bond.

X₁ and X₂ in Formula 1 may each independently be N or C.

In one embodiment, in Formula 1, X₁ and X₂ may each be N, and the bondbetween X₁ and M and the bond between X₂ and M may each be a coordinatebond, but embodiments of the present disclosure are not limited thereto.

For example, in Formula 1, X₁ may be C, X₂ may be N, the bond between X₁and M may be a covalent bond, and the bond between X₂ and M may be acoordinate bond. For example, X₁ may be N, X₂ may be C, the bond betweenX₁ and M may be a coordinate bond, and the bond between X₂ and M may bea covalent bond.

A₁ to A₄ in Formula 1 may each independently be a C₅-C₃₀ carbocyclicgroup or a C₁-C₆₀ heterocyclic group.

In one embodiment, A₁ to A₄ in Formula 1 may each independently beselected from:

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a phenalene group, a tetracene group, a chrysenegroup, a pyrene group, a fluoranthene group, a triphenylene group, afluorene group, a benzofluorene group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, an indole group, aniso-indole group, an indazole group, a quinoline group, an isoquinolinegroup, a benzoquinoline group, a phthalazine group, a naphthyridinegroup, a quinoxaline group, a quinazoline group, a cinnoline group, acarbazole group, a phenanthridine group, an acridine group, aphenanthroline group, a phenazine group, a benzimidazole group, atriazine group, a benzocarbazole group, and a dibenzocarbazole group,but embodiments of the present disclosure are not limited thereto.

For example, A₁ to A₄ may each independently be selected from a benzenegroup, a naphthalene group, a pyridine group, a pyrimidine group, apyrazine group, a triazine group, a quinoline group, and an isoquinolinegroup.

In one embodiment, A₁ to A₄ may be identical to or different from eachother.

For example, A₁ and A₂ may be identical to each other. For example, A₁and A₂ may be different from each other. For example, A₃ and A₄ may beidentical to each other. For example, A₃ and A₄ may be different fromeach other. For example, A₁ may be different from A₃ and A₄. Forexample, A₂ may be different from A₃ and A₄.

In one embodiment, A₁ and A₂ may each independently be selected from apyridine group, a pyridine group, a pyrimidine group, a pyrazine group,a triazine group, a quinoline group, and an isoquinoline group.

A₃ and A₄ may each independently be a benzene group or a naphthalenegroup, but embodiments of the present disclosure are not limitedthereto.

T₁ and T₂ in Formula 1 may each independently be selected from*—N[(L₁₁)_(a11)-(R₁₁)_(b11)]—*′, *—B(R₁₁)—*′, *—P(R₁₁)—*′,*—C(R₁₁)(R₁₂)—*′, *—Si(R₁₁)(R₁₂)—*, *—Ge(R₁₁)(R₁₂)—*′, *—S—*′, *—Se—*′,*—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₁₁)═*′, *═C(R₁₁)—*′,*—C(R₁₁)═C(R₁₂)—*′, *—C(═S)—*′, and *—C≡C—*′.

L₁₁ may be a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, L₁₁ may be selected from:

a benzene group, a naphthalene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, an indole group, an iso-indole group, an indazole group, a purinegroup, a quinoline group, an isoquinoline group, a naphthyridine group,a quinoxaline group, a quinazoline group, a cinnoline group, abenzimidazole group, a benzofuran group, a benzothiophene group, aniso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, and a triazinegroup; and

a benzene group, a naphthalene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, an indole group, an iso-indole group, an indazole group, a purinegroup, a quinoline group, an isoquinoline group, a naphthyridine group,a quinoxaline group, a quinazoline group, a cinnoline group, abenzimidazole group, a benzofuran group, a benzothiophene group, aniso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, and a triazinegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, and a triazinyl group, butembodiments of the present disclosure are not limited thereto.

a11 may be selected from 0 to 3, wherein, when a11 is zero,*-(L₁₁)_(a11)-*′ may be a single bond.

When a11 is two or more, two or more L₁₁(s) may be identical to ordifferent from each other.

R₁₁ and R₁₂ may optionally be linked to a neighboring substituent in R₁to R₃ to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group.

a1 and a2 in Formula 1 may each independently be 0, 1, 2, or 3, wherein,when a1 is zero, *-(T₁)_(a1)-*′ may be a single bond, and when a2 iszero, *-(T₂)_(a2)-*′ may be a single bond.

When a1 is two or more, two or more T₁(s) may be identical to ordifferent from each other, and when a2 is two or more, two or more T₂(s)may be identical to or different from each other.

R₁ to R₄, R₁₁, and R₁₂ in Formula 1 may each independently be selectedfrom:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂).

In one embodiment, R₁ to R₄, R₁₁, and R₁₂ in Formula 1 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, anda C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, an anthracenylgroup, a phenanthrenyl group, a phenalenyl group, a tetracenyl group, achrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenylgroup, a fluorenyl group, a benzofluorenyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, atriazinyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group;and

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, an anthracenylgroup, a phenanthrenyl group, a phenalenyl group, a tetracenyl group, achrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenylgroup, a fluorenyl group, a benzofluorenyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, atriazinyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a phenalenyl group,a tetracenyl group, a chrysenyl group, a pyrenyl group, a fluoranthenylgroup, a triphenylenyl group, a fluorenyl group, a benzofluorenyl group,a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, a triazinyl group, a benzocarbazolyl group, adibenzocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂), but embodiments of the present disclosure are notlimited thereto.

Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₂₀aryl group, a C₁-C₂₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group, but embodiments of the present disclosure arenot limited thereto.

For example, R₁ to R₄, R₁₁, and R₁₂ in Formula 1 may each independentlybe selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, anda C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, and a benzimidazolyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, and a benzimidazolyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzimidazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂), and

Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₂₀aryl group, a C₁-C₂₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

For example, R₁ to R₄, R₁₁, and R₁₂ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₁-C₂₀ alkoxy group, and groups represented by Formulae 5-1 to5-16:

In Formulae 5-1 to 5-16,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇),

Z₃₁ to Z₃₇ may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, afluorenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, acarbazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolylgroup, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group,

e2 may be an integer from 0 to 2,

e3 may be an integer from 0 to 3,

e4 may be an integer from 0 to 4,

e5 may be an integer from 0 to 5,

e6 may be an integer from 0 to 6,

e7 may be an integer from 0 to 7, and

* indicates a binding site to a neighboring atom.

Neighboring substituents in R₁ to R₄ in Formula 1 may optionally belinked to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, when two or more R₁(s) are present, two or moreneighboring R₁(s) may be linked to form a substituted or unsubstitutedC₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group. Similarly, when two or more R₂(s), R₃(s), or R₄(s)are present, two or more neighboring R₂(s), R₃(s), or R₄(s) may belinked to form a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₆₀ heterocyclic group.

b1 to b4 and b11 in Formula 1 may each independently be selected from 1to 6, wherein, when b1 is two or more, two or more R₁(s) may beidentical to or different from each other, when b2 is two or more, twoor more R₂(s) may be identical to or different from each other, when b3is two or more, two or more R₃(s) may be identical to or different fromeach other, and when b4 is two or more, two or more R₄(s) may beidentical to or different from each other.

In Formula 1, a moiety represented by

may be identical to a moiety represented by

In Formula 1,

may be represented by Formula 2-1, and

may be represented by Formula 2-2 or Formula 2-3:

In Formulae 2-1 to 2-3,

X₁, X₂, R₁, R₂, b1, and b2 are the same as described above,

* and *′ respectively indicate binding sites to T₁ and T₂ in Formula 1,and *″ indicates a binding site to M in Formula 1, and

Y₁ to Y₄, Y₁₁ to Y₁₃, and Y₂₁ to Y₂₇ may each independently be C or N.

In one embodiment, in Formulae 2-1 to 2-3,

X₁ and X₂ may each be N, and

Y₁ to Y₄, Y₁₁ to Y₁₃, and Y₂₁ to Y₂₇ may each be C.

In Formula 1,

a moiety represented by

may be selected from groups represented by Formulae 2-4 to 2-8:

In Formulae 2-4 to 2-8, * indicates a binding site to T₁ in Formula 1,and *″ indicates a binding site to M in Formula 1, and

R₃, R₄, b3, and b4 are the same as described above.

In Formula 1,

may be selected from groups represented by Formulae 2-1(1) to 2-1(3):

In Formulae 2-1(1) to 2-1(3), * indicates a binding site to T₁ inFormula 1, *′ indicates a binding site to T₂ in Formula 1, and *″indicates a binding site to M in Formula 1, and

R₁ and b1 are the same as described above.

In one embodiment, R₁ in Formulae 2-1(1) to 2-1(3) may be selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀alkoxy group, and groups represented by Formulae 5-1 to 5-16.

L₁ in Formula 1 may be a monovalent organic ligand. The term “monovalentorganic ligand” as used herein refers to a ligand having one bindingsite to a center metal in an organic compound.

In one embodiment, L₁ may be selected from groups represented byFormulae 3L-1 to 3L-4, but embodiments of the present disclosure are notlimited thereto:

In Formulae 3L-1 to 3L-4,

Z₁₁ and Z₁₂ may each independently be selected from:

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a phenalene group, a tetracene group, a chrysenegroup, a pyrene group, a fluoranthene group, a triphenylene group, afluorene group, and a benzofluorene group; and

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a phenalene group, a tetracene group, a chrysenegroup, a pyrene group, a fluoranthene group, a triphenylene group, afluorene group, and a benzofluorene group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

c11 and c12 may each independently be selected from 0 to 3, wherein,when c11 is zero, *—(Z₁₁)_(c11)—*′ may be a single bond, and when c12 iszero, *—(Z₁₂)_(c12)—*′ may be a single bond,

L₁₂ to L₁₄ are the same as described in connection with L₁₁,

a12 to a14 are the same as described in connection with a11,

Ar₁₁ to Ar₁₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group,

X₁₁ may be selected from —F, —Cl, —Br, and —I,

* indicates a binding site to M in Formula 1,

at least one substituent of the substituted C₃-C₁₀ cycloalkyl group, thesubstituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, thesubstituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroarylgroup, the substituted monovalent non-aromatic condensed polycyclicgroup, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

For example, L₁ in Formula 1 may be selected from groups represented byFormulae 3L(1) to 3L(15):

The organometallic compound represented by Formula 1 may be one ofCompounds 1 to 76, but embodiments of the present disclosure are notlimited thereto:

The organometallic compound represented by Formula 1 has a structure inwhich a transition metal (e.g., Pd or Pt) capable of forming afour-coordinate structure is included as a center metal and the centermetal is linked to a tridentate ligand and a monodentate ligand. Becausethe ligand includes at least one electron donating group moiety, highestoccupied molecular orbital (HOMO) of the organometallic compound may befurther increased due to a strong electron donation, thus securing amaterial (e.g., with an emission wavelength) shifted to a near-infrared(NIR) region by a long wavelength.

For example, because the organometallic compound represented by Formula1 includes a carbazole group in a tridentate ligand, the long wavelengthshift effect is excellent, thereby facilitating the design of a materialhaving a desired wavelength, as compared with the case in which theorganometallic compound has a phenyl group (e.g., in place of thecarbazole group).

A synthesis method for the organometallic compound represented byFormula 1 would be apparent to those of ordinary skill in the art byreferring to the following examples.

At least one of the organometallic compounds of Formula 1 may beutilized between a pair of electrodes of an organic light-emittingdevice. For example, the organometallic compound may be included in anemission layer. In one or more embodiments, the organometallic compoundof Formula 1 may be utilized as a material for a capping layer locatedoutside of a pair of electrodes of an organic light-emitting device.

Accordingly, an organic light-emitting device is provide to include: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode, theorganic layer including an emission layer, wherein the organic layerincludes at least one organometallic compound.

The expression “(an organic layer) includes at least one organometalliccompound” as used herein may include a case in which “(an organic layer)includes identical compounds represented by Formula 1” and a case inwhich “(an organic layer) includes two or more different organometalliccompounds.”

In one embodiment, the first electrode is an anode, and the secondelectrode is a cathode, and the organic layer further includes a holetransport region between the first electrode and the emission layer andan electron transport region between the emission layer and the secondelectrode, and the hole transport region includes a hole injectionlayer, a hole transport layer, an emission auxiliary layer, an electronblocking layer, or any combination thereof, and the electron transportregion includes a buffer layer, a hole blocking layer, an electroncontrol layer, an electron transport layer, an electron injection layer,or any combination thereof.

In one or more embodiments, the emission layer may include theorganometallic compound represented by Formula 1.

In one embodiment, the organometallic compound may have a maximumemission wavelength in a range of about 700 nm to about 1,100 nm. Forexample, the emission layer including at least one of the organometalliccompound may have a maximum emission wavelength in a range of about 700nm to about 1,100 nm.

In one embodiment, the emission layer may further include a host, and anamount of the host may be greater than that of the organometalliccompound.

The hole transport region may include a p-dopant, and the p-dopant mayinclude a cyano group-containing compound described below.

In the organic light-emitting device, the emission layer may be a firstcolor light emission layer, wherein

the organic light-emitting device may further include i) at least onesecond color light emission layer or ii) at least one second color lightemission layer and at least one third color light emission layer,between the first electrode and the second electrode,

a maximum emission wavelength of the first color light, a maximumemission wavelength of the second color light, and a maximum emissionwavelength of the third color light may be identical to or differentfrom each other, and

the first color light and the second color light may be emitted in theform of mixed light, or the first color light, the second color light,and the third color light may be emitted in the form of mixed light.

The organic light-emitting device may further include at least oneselected from a first capping layer disposed in a pathway along whichlight generated in an emission layer proceeds toward the outside throughthe first electrode and a second capping layer disposed in a pathwayalong which light generated in an emission layer proceeds toward theoutside through the second electrode, and at least one selected from thefirst capping layer and the second capping layer may include at leastone organometallic compound represented by Formula 1.

For example, the organic light-emitting device may have i) a stackedstructure including a first electrode, an organic layer, a secondelectrode, and a second capping layer which are sequentially stacked inthis stated order, ii) a stacked structure including a first cappinglayer, a first electrode, an organic layer, and a second electrode whichare sequentially stacked in this stated order, or iii) a stackedstructure including a first capping layer, a first electrode, an organiclayer, a second electrode, and a second capping layer which aresequentially stacked in this stated order, and at least one selectedfrom the first capping layer and the second capping layer may includethe organometallic compound.

In one embodiment, there is provided an electronic device including athin film transistor and the organic light-emitting device, wherein thethin film transistor may include a source electrode, a drain electrode,an activation layer, and a gate electrode, and the first electrode ofthe organic light-emitting device may be electrically connected with atleast one of the source electrode and the drain electrode of the thinfilm transistor. In one embodiment, there is provided an electronicdevice including a thin film transistor including a source electrode, adrain electrode, an activation layer, and a gate electrode, wherein thefirst electrode of the organic light-emitting device may be electricallyconnected with one of the source electrode and the drain electrode ofthe thin film transistor.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of the organic light-emitting device. A materialincluded in the “organic layer” is not limited to an organic material.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. The organic light-emitting device 10includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and/or water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for the first electrodemay be selected from materials with a high work function to facilitatehole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming thefirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, a material forforming the first electrode may be selected from magnesium (Mg), silver(Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

Organic Layer 150

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer, and an electrontransport region between the emission layer and the second electrode190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in the respective stated order, but the structure of thehole transport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may be optionally linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one or more embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, in Formula 201, at least one selected fromR₂₀₁ to R₂₀₃ may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group, but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, in Formula 202, at least one selected fromR₂₀₁ to R₂₀₄ may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

For example, the compound represented by Formula 201 may be representedby Formula 201A(1), but embodiments of the present disclosure are notlimited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ are the same as described in connection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, a thickness of the hole injection layer maybe in a range of about 100 Å to about 9,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may be ina range of about 50 Å to about 2,000 Å, for example about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

P-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant has a lowest unoccupied molecularorbital (LUMO) level of about −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221 below,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

An amount of the dopant in the emission layer may be typically in arange of about 0.01 part to about 15 parts by weight based on 100 partsby weight of the host, but embodiments of the present disclosure are notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within these ranges, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Host in Emission Layer

In one or more embodiments, the host may include a compound representedby Formula 301 below.[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, in Formula 301, Ar₃₀₁ may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

In Formula 301, when xb11 is two or more, two or more Ar₃₀₁(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or Formula 301-2:

In Formulae 301-1 to 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, abenzonaphthothiophene group, and a dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described above,

L₃₀₂ to L₃₀₄ may each independently be the same as described inconnection with L₃₀₁,

Xb2 to xb4 may each independently be the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as described inconnection with R₃₀₁.

For example, in Formulae 301, 301-1 and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one π electron-depleted nitrogen-containingring.

The term “π electron-depleted nitrogen-containing ring” as used hereinrefers to a C₁-C₆₀ heterocyclic group having at least one *—N═*′ moietyas a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 7-membered to a 60-membered heteromonocyclic group having at leastone *—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring include animidazole group, a pyrazole group, a thiazole group, an isothiazolegroup, an oxazole group, an isoxazole group, a pyridine group, apyrazine group, a pyrimidine group, a pyridazine group, an indazolegroup, a purine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a phthalazine group, a naphthyridine group, aquinoxaline group, a quinazoline group, a cinnoline group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, an iso-benzothiazole group, abenzoxazole group, an isobenzoxazole group, a triazole group, atetrazole group, an oxadiazole group, a triazine group, a thiadiazolegroup, an imidazopyridine group, an imidazopyrimidine group, and anazacarbazole group, but embodiments of the present disclosure are notlimited thereto.

The electron transport region may include a compound represented byFormula 601:[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)—  Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀1(s) in the number of xe11 and/orat least one of R₆₀₁(s) in the number of xe21 may include the πelectron-depleted nitrogen-containing ring.

In one embodiment, in Formula 601, ring Ar₆₀₁ may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In Formula 601, when xe1 is two or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, in Formula 601, Ar₆₀₁ may be an anthracenegroup.

In one or more embodiments, the compound represented by Formula 601 maybe represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁,

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, in Formulae 601 and 601-1, L₆₀₁ and L₆₁₁ to L₆₁₃ mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group, but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, in Formulae 601 and 601-1, xe1 and xe611 toxe613 may each independently be 0, 1, or 2.

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ toR₆₁₃ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one compound selected from2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

A thickness of the buffer layer, the hole blocking layer, or theelectron control layer may be in a range of about 20 Å to about 1,000 Å,for example, about 30 Å to about 300 Å. When the thicknesses of thebuffer layer, the hole blocking layer, and the electron control layerare within these ranges, the electron blocking layer may have excellentelectron blocking characteristics or electron control characteristicswithout a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangesdescribed above, the electron transport layer may have satisfactoryelectron transport characteristics without a substantial increase indriving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenylthiadiazol, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, and/or K₂O, and alkali metal halides, such as LiF, NaF,CsF, KF, LiI, NaI, CsI, and/or KI. In one embodiment, the alkali metalcompound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1),and/or Ba_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkalineearth-metal compound may be selected from BaO, SrO, and CaO, butembodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazol,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (e.g., may consist of) analkali metal, an alkaline earth metal, a rare earth metal, an alkalimetal compound, an alkaline earth-metal compound, a rare earth metalcompound, an alkali metal complex, an alkaline earth-metal complex, arare earth metal complex, or any combinations thereof, as describedabove. In one or more embodiments, the electron injection layer mayfurther include an organic material. When the electron injection layerfurther includes an organic material, an alkali metal, an alkaline earthmetal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof may be homogeneously or non-homogeneouslydispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the ranges describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

Second Electrode 190

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

An organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, and a secondelectrode 190 which are sequentially stacked in this stated order, anorganic light-emitting device 30 of FIG. 3 includes a first electrode110, an organic layer 150, a second electrode 190, and a second cappinglayer 220 which are sequentially stacked in this stated order, and anorganic light-emitting device 40 of FIG. 4 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, a secondelectrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer 210 toward theoutside, and in the organic layer 150 of each of the organiclight-emitting devices 30 and 40, light generated in an emission layermay pass through the second electrode 190, which is a semi-transmissiveelectrode or a transmissive electrode, and the second capping layer 220toward the outside.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selectedfrom the first capping layer 210 and the second capping layer 220 mayeach independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto:

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1-4. However,embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, the emission layer, andlayers constituting the electron transport region may be formed in acertain region by utilizing one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, the emission layer,and layers constituting the electron transport region are formed byvacuum deposition, for example, the vacuum deposition may be performedat a deposition temperature of about 100 to about 500° C., at a vacuumdegree of about 10⁻⁸ to about 10⁻³ torr, and at a deposition rate ofabout 0.01 to about 100 Å/sec by taking into account a material to beincluded in a layer to be formed, and the structure of a layer to beformed.

When layers constituting the hole transport region, the emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2000 rpm to about 5000 rpm and at a heat treatment temperature of about80° C. to 200° C. by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

Apparatus

The organic light-emitting device may be included in a variety ofapparatuses. For example, a light-emitting apparatus, an authenticationapparatus, or an electronic apparatus including the organiclight-emitting device may be provided.

The light-emitting apparatus may further include, in addition to theorganic light-emitting device, a thin film transistor including a sourceelectrode and a drain electrode. One of the source electrode and thedrain electrode of the thin film transistor may be electricallyconnected to one of the first electrode and the second electrode of theorganic light-emitting device. The light-emitting apparatus may beutilized as various displays, light sources, and/or the like.

The authentication apparatus may be, for example, a biometricauthentication apparatus for authenticating an individual by utilizingbiometric information of a biometric body (for example, a finger tip, apupil, and/or the like).

The authentication apparatus may further include, in addition to theorganic light-emitting device, a biometric information collector.

The electronic apparatus may be applied to personal computers (forexample, a mobile personal computer), mobile phones, digital cameras,electronic organizers, electronic dictionaries, electronic gamemachines, medical instruments (for example, electronic thermometers,sphygmomanometers, blood glucose meters, pulse measurement devices,pulse wave measurement devices, electrocardiogram (ECG) displays,ultrasonic diagnostic devices, and/or endoscope displays), fish finders,various measuring instruments, meters (for example, meters for avehicle, an aircraft, and a vessel), projectors, and/or the like, butembodiments of the present disclosure are not limited thereto.

General Definition of Substituents

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same (or substantially the same) structure as theC₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one double bond in the middle or at the terminusof the C₂-C₆₀ alkyl group, and examples thereof include an ethenylgroup, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having thesame (or substantially the same) structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one triple bond in the middle or at the terminusof the C₂-C₆₀ alkyl group, and examples thereof include an ethynylgroup, and a propynyl group. The term “C₂-C₆₀ alkynylene group” as usedherein refers to a divalent group having the same (or substantially thesame) structure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term“C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent grouphaving the same (or substantially the same) structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having the same (or substantially the same) structure as theC₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone double bond in the ring thereof and no aromaticity, and examplesthereof include a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” as usedherein refers to a divalent group having the same (or substantially thesame) structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one double bond in its ring. Non-limiting examples of theC₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the same (orsubstantially the same) structure as the C₁-C₁₀ heterocycloalkenylgroup.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a heterocyclic aromaticsystem that has at least one heteroatom selected from N, O, P, and S asa ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limitingexamples of the C₁-C₆₀ heteroaryl group include a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group each include two ormore rings, the rings may be condensed with each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to a grouprepresented by —OA₁₀₂ (wherein A₁₀₂ is the C₆-C₆₀ aryl group), and theterm “C₆-C₆₀ arylthio group” as used herein refers to a grouprepresented by —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. A detailed example of the monovalent non-aromatic condensedpolycyclic group is a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same (or substantially the same) structure as the monovalentnon-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure. An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein refers toa divalent group having the same (or substantially the same) structureas the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which thering-forming atoms include only carbon atoms. The C₅-C₆₀ carbocyclicgroup may be an aromatic carbocyclic group or a non-aromatic carbocyclicgroup. The C₅-C₆₀ carbocyclic group may be a ring (such as benzene), amonovalent group (such as a phenyl group), or a divalent group (such asa phenylene group). In one or more embodiments, depending on the numberof substituents connected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving the same (or substantially the same) structure as the C₁-C₆₀carbocyclic group, except that as a ring-forming atom, at least oneheteroatom selected from N, O, Si, P, and S is used in addition tocarbon (the number of carbon atoms may be in a range of 1 to 60).

At least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph” as used herein may refer to a phenyl group; the term “Me”as used herein may refer to a methyl group; the term “Et” as used hereinmay refer to an ethyl group; the terms “ter-Bu” or “But” as used hereinmay refer to a tert-butyl group; and the term “OMe” as used herein mayrefer to a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′ as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The expression“B was utilized instead of A” utilized in describing Synthesis Examplesrefers to that an identical number of molar equivalents of B wasutilized in place of molar equivalents of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound 35

Synthesis of Compound 1-2

2 g (8.5 mmol) of Compound 1-1, 2.15 g (10.2 mmol) of1-carbazolylboronic acid, 1.0 g (25.5 mmol) of NaOH, 0.5 g (0.4 mmol) ofPd(PPh₃)₄, 30 ml of 1,4-dioxane, and 8 ml of H₂O were mixed in anitrogen atmosphere and then stirred at a temperature of 100° C. for 12hours. The mixture obtained after the reaction was completed wasextracted therefrom by utilizing ethyl acetate, dried by utilizingMgSO₄, and then filtered to obtain an organic layer. A solvent wasremoved from the organic layer, and column chromatography was performedthereon to obtain 1.8 g (yield: 66%) of Compound 1-2.

Synthesis of Compound 35

0.5 g (1.6 mmol) of Compound 1-2, 0.7 g (1.7 mmol) of K₂PtCl₄, and 40 mlof acetic acid were mixed in a nitrogen atmosphere and then stirred at atemperature of 130° C. for 48 hours. A solid obtained after the reactionwas completed was filtered, washed by utilizing methanol, water, anddiethyl ether, and recrystallized by utilizing dichloromethane to obtain0.3 g (yield: 34%) of Compound 35.

Synthesis Example 2 to 4: Synthesis of Compounds 1, 18, and 37

Synthesis of Compound 1

0.3 g (0.5 mmol) of Compound 35, and 5 ml of tetrahydrofuran (THF) weremixed in a nitrogen atmosphere, and 1.5 ml of phenylmagnesium bromidewas added dropwise thereto. Then, the mixture was stirred at atemperature of 20° C. for 6 hours. The mixture obtained after thereaction was completed was extracted therefrom by utilizingdichloromethane, dried by utilizing MgSO₄, and then filtered to obtainan organic layer. A solvent was removed from the organic layer, andcolumn chromatography was performed thereon to obtain 0.2 g (yield: 62%)of Compound 1.

Synthesis of Compound 18

0.15 g (yield: 47%) of Compound 18 was synthesized in the same (orsubstantially the same) manner as in Synthesis of Compound 1, exceptthat (4-(diphenylamino)phenyl)magnesium bromide was utilized instead ofphenylmagnesium bromide.

Synthesis of Compound 37

0.3 g (0.5 mmol) of Compound 35 and 20 ml of acetone were mixed in anitrogen atmosphere, and 127 mg (0.75 mmol) of sodium phenoxidetrihydrate was dissolved in 20 ml of methanol and added dropwise to themixture. Then, the mixture was stirred at room temperature for 10minutes and stirred for 3 hours while applying heat thereto. A solidobtained after the reaction was completed was filtered, washed byutilizing methanol, water, and diethyl ether, and recrystallized byutilizing dichloromethane to obtain 0.17 g (yield: 55%) of Compound 37.

Synthesis methods of compounds other than Compounds shown in Table 1 mayalso be easily recognized by those of ordinary skill in the art byreferring to the synthesis mechanisms and source materials describedabove.

Example 1

As a substrate and an ITO anode, a Corning 15 Ω/cm² (120 nm) ITO glasssubstrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated withisopropyl alcohol and pure water each for 5 minutes, and then cleaned byexposure to ultraviolet rays and ozone for 30 minutes. The ITO glasssubstrate was provided to a vacuum deposition apparatus.

HT and HAT-CN were co-deposited on the ITO anode formed on the ITO glasssubstrate at a weight ratio of 99:1 to form a hole transport layerhaving a thickness of 120 nm.

H-1 (host) and Compound 1 (dopant) were co-deposited on the holetransport layer at a host to dopant weight ratio of 98:2 to form anemission layer having a thickness of 30 nm.

ET1 was deposited on the emission layer to form a first electrontransport layer having a thickness of 5 nm, ET2 was deposited on thebuffer layer to form a second electron transport layer having athickness of 25 nm, LiF was deposited on the electron transport layer toform an electron injection layer having a thickness of 0.5 nm, and Alwas vacuum-deposited on the electron injection layer to form a cathodehaving a thickness of 3,000 Å, thereby completing the manufacture of anorganic light-emitting device.

Examples 2 and 3 and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compoundsshown in Table 1 were each utilized instead of Compound 1 in forming anemission layer.

TABLE 1 Maximum emission Dopant wavelength (λ_(max)) Example 1 Compound1 821 nm Example 2 Compound 18 880 nm Example 3 Compound 37 835 nmComparative Compound A 543 nm Example 1 Comparative Compound B 530 nmExample 2 Compound A

Compound B

TABLE 2 Maximum emission Dopant Relative efficiency wavelength (λ_(max))Example 1 Compound 1 135% 821 nm Example 2 Compound 18 102% 880 nmExample 3 Compound 37 120% 835 nm Comparative Compound C 100% 770 nmExample 3 Compound C

Referring to Table 1, it is confirmed that the organic light-emittingdevices of Examples 1 to 3 exhibit a maximum emission wavelength of(e.g., in) a near-infrared region, while the organic light-emittingdevices of Comparative Examples 1 and 2 emit green light of 500 nm in avisible region.

Referring to Table 2, it is confirmed that the organic light-emittingdevices of Examples 1 to 3 exhibit high efficiency, as compared with theorganic light-emitting device of Comparative Example 3.

Organic light-emitting devices including such organometallic compoundsare capable of emitting light of a near-infrared region while having lowdriving voltage, high efficiency, and long lifespan characteristics.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various suitable changes in form and details may be made thereinwithout departing from the spirit and scope as defined by the followingclaims, and equivalents thereof.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein, in Formula 1, M is a transition metal, L₁ is a monovalentorganic ligand, two bonds selected from a bond between X₁ and M, a bondbetween X₂ and M, and a bond between L₁ and M are each a coordinatebond, and a third bond thereof is a covalent bond, X₁ and X₂ are eachindependently N or C, A₁ to A₄ are each independently a C₅-C₃₀carbocyclic group or a C₁-C₆₀ heterocyclic group, T₁ and T₂ are eachindependently selected from *—N[(L₁₁)_(a11)-(R₁₁)_(b11)]—*′,*—B(R₁₁)—*′, *—P(R₁₁)—*′, *—C(R₁₁)(R₁₂)—*′, *—Si(R₁₁)(R₁₂)—*′,*—Ge(R₁₁)(R₁₂)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′,*—S(═O)₂—*′, *—C(R₁₁)=*′, *═C(R₁₁)*′, *—C(R₁₁)═C(R₁₂)—*′, *—C(═S)—*′,and *—C≡C—*′, L₁₁ is a single bond, a substituted or unsubstitutedC₅-C₃₀ carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group, a11 is selected from 0 to 3, wherein, when a11 iszero, *-(L₁₁)_(a11)-*′ is a single bond, when a11 is two or more, two ormore L₁₁(s) are identical to or different from each other, R₁₁ and R₁₂are optionally linked to a neighboring substituent in R₁ to R₃ to form asubstituted or unsubstituted C₅-C₃₀ carbocyclic group or a substitutedor unsubstituted C₁-C₆₀ heterocyclic group, a1 and a2 are eachindependently 0, 1, 2, or 3, wherein, when a1 is zero, *-(T₁)_(a1)-*′ isa single bond, and when a2 is zero, *-(T₂)_(a2)-*′ is a single bond,when a1 is two or more, two or more T₁(s) are identical to or differentfrom each other, and when a2 is two or more, two or more T₂(s) areidentical to or different from each other, R₁ to R₄, R₁₁, and R₁₂ areeach independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), neighboringsubstituents in R₁ to R₄ are optionally linked to form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group, b1 to b4 and b11 are each independentlyselected from 1 to 6, wherein, when b1 is two or more, two or more R₁(s)are identical to or different from each other, when b2 is two or more,two or more R₂(s) are identical to or different from each other, when b3is two or more, two or more R₃(s) are identical to or different fromeach other, and when b4 is two or more, two or more R₄(s) are identicalto or different from each other, and when b11 is two or more, two ormore R₁₁(s) are identical to or different from each other, at least onesubstituent of the substituted C₅-C₃₀ carbocyclic group, the substitutedC₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, abiphenyl group, and a terphenyl group; a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ toQ₂₃, and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.
 2. Theorganometallic compound of claim 1, wherein M in Formula 1 is selectedfrom Zn, Cu, Pt, and Pd.
 3. The organometallic compound of claim 1,wherein X₁ and X₂ in Formula 1 are each N, and the bond between X₁ and Mand the bond between X₂ and M are each a coordinate bond.
 4. Theorganometallic compound of claim 1, wherein A₁ to A₄ in Formula 1 areeach independently selected from a benzene group, a naphthalene group,an anthracene group, a phenanthrene group, a phenalene group, atetracene group, a chrysene group, a pyrene group, a fluoranthene group,a triphenylene group, a fluorene group, a benzofluorene group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, an indole group, an isoindole group, an indazole group, aquinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a carbazole group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, a triazine group, abenzocarbazole group, and a dibenzocarbazole group.
 5. Theorganometallic compound of claim 1, wherein A₁ and A₂ in Formula 1 areidentical to each other.
 6. The organometallic compound of claim 1,wherein A₁ and A₂ are each independently selected from a pyridine group,a pyrimidine group, a pyrazine group, a triazine group, a quinolinegroup, and an isoquinoline group, and A₃ and A₄ are each independently abenzene group or a naphthalene group.
 7. The organometallic compound ofclaim 1, wherein R₁ to R₄, R₁₁, and R₁₂ in Formula 1 are eachindependently selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, and a C₁-C₂₀ alkoxy group; aC₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; acyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, an anthracenylgroup, a phenanthrenyl group, a phenalenyl group, a tetracenyl group, achrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenylgroup, a fluorenyl group, a benzofluorenyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, atriazinyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group;a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, an anthracenylgroup, a phenanthrenyl group, a phenalenyl group, a tetracenyl group, achrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenylgroup, a fluorenyl group, a benzofluorenyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, atriazinyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a phenalenyl group,a tetracenyl group, a chrysenyl group, a pyrenyl group, a fluoranthenylgroup, a triphenylenyl group, a fluorenyl group, a benzofluorenyl group,a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, a triazinyl group, a benzocarbazolyl group, adibenzocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), andQ₁ to Q₃ and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₂₀ arylgroup, a C₁-C₂₀ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.
 8. The organometallic compound of claim 1,wherein, in Formula 1, a moiety represented by

is identical to a moiety represented by


9. The organometallic compound of claim 1, wherein, in Formula 1,

is represented by Formula 2-1, and

is represented by Formula 2-2 or Formula 2-3:

wherein, in Formulae 2-1 to 2-3, X₁, X₂, R₁, R₂, b1, and b2 are the sameas described in Formula 1, * and *′ each indicate a binding site to T₁or T₂ in Formula 1, and *″ indicates a binding site to M in Formula 1,and Y₁ to Y₄, Y₁₁ to Y₁₃, and Y₂₁ to Y₂₇ are each independently C or N.10. The organometallic compound of claim 1, wherein, in Formula 1, amoiety represented by

is selected from groups represented by Formulae 2-4 to 2-8:

wherein, in Formulae 2-4 to 2-8, * indicates a binding site to T₁ inFormula 1, and *″ indicates a binding site to M in Formula 1, and R₃,R₄, b3, and b4 are the same as described in Formula
 1. 11. Theorganometallic compound of claim 1, wherein, in Formula 1,

is selected from groups represented by Formulae 2-1(1) to 2-1(3):

wherein, in Formulae 2-1(1) to 2-1(3), * indicates a binding site to T₁in Formula 1, *′ indicates a binding site to T₂ in Formula 1, and *″indicates a binding site to M in Formula 1, and R₁ and b1 are the sameas described in Formula
 1. 12. The organometallic compound of claim 1,wherein L₁ in Formula 1 is selected from groups represented by Formulae3L-1 to 3L-4:

wherein, in Formulae 3L-1 to 3L-4, Z₁₁ and Z₁₂ are each independentlyselected from: a benzene group, a naphthalene group, an anthracenegroup, a phenanthrene group, a phenalene group, a tetracene group, achrysene group, a pyrene group, a fluoranthene group, a triphenylenegroup, a fluorene group, and a benzofluorene group; and a benzene group,a naphthalene group, an anthracene group, a phenanthrene group, aphenalene group, a tetracene group, a chrysene group, a pyrene group, afluoranthene group, a triphenylene group, a fluorene group, and abenzofluorene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group, c11 and c12 are eachindependently selected from 0 to 3, wherein, when c11 is zero,*—(Z₁₁)_(c11)—*′ is a single bond, and when c12 is zero,*—(Z₁₂)_(c12)—*′ is a single bond, L₁₂ to L₁₄ are the same as describedin connection with L₁₁ in Formula 1, a12 to a14 are the same asdescribed in connection with a11 in Formula 1, Ar₁₁ to Ar₁₄ are eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,X₁₁ is selected from F, Cl, Br, and I, * indicates a binding site to Min Formula 1, at least one substituent of the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group, thesubstituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group is selected from:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂), and Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 13. The organometallic compound of claim1, wherein the organometallic compound is represented by one ofCompounds 1 to 76:


14. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, the organic layercomprising an emission layer and at least one of the organometalliccompound of claim
 1. 15. The organic light-emitting device of claim 14,wherein the first electrode is an anode, the second electrode is acathode, and the organic layer comprises i) a hole transport regionbetween the first electrode and the emission layer, the hole transportregion comprising a hole injection layer, a hole transport layer, abuffer layer, an electron blocking layer, or a combination thereof andii) an electron transport region between the emission layer and thesecond electrode, the electron transport region comprising a holeblocking layer, an electron transport layer, an electron injectionlayer, or a combination thereof.
 16. The organic light-emitting deviceof claim 14, wherein the emission layer comprises the at least one oforganometallic compound.
 17. The organic light-emitting device of claim16, wherein the organometallic compound has a maximum emissionwavelength in a range of about 700 nm to about 1,100 nm.
 18. The organiclight-emitting device of claim 16, wherein the emission layer furthercomprises a host, and an amount of the host is larger than an amount ofthe organometallic compound.
 19. An apparatus comprising the organiclight-emitting device of claim
 14. 20. The apparatus of claim 19,wherein the apparatus is a light-emitting apparatus, an authenticationapparatus, or an electronic apparatus.